Another thing to consider - if any single person donated more than $17,000 to you in 2023, THEY might need to file a gift tax return (Form 709). This doesn't affect you as the recipient though, and doesn't mean the gift becomes taxable to you. It's just a reporting requirement for large gifts from the donor's side.

I'm so sorry for what you and your family are going through. Having dealt with similar fundraising during my grandmother's final months, I completely understand the stress of wondering about tax implications on top of everything else. The good news is that what you received are indeed gifts, not taxable income. Since you're well under the $20,000 and 200 transaction thresholds for 1099-K reporting, the platforms won't be sending you any tax forms. You don't need to report these donations as income on your tax return. However, I'd strongly recommend keeping detailed records of all donations received and how the funds were used - bank statements, screenshots of the fundraising pages, receipts for medical expenses, etc. This documentation will be invaluable if you ever need to explain these deposits to the IRS. The fact that your friend initially set up the GoFundMe shouldn't be an issue as long as it was clearly for personal medical expenses and the funds came directly to you. Just make sure it wasn't accidentally set up as a charitable organization fundraiser. You're smart to consult with your family's CPA before filing season. They'll be able to review your specific situation and provide peace of mind. Take care of yourself during this difficult time.

Whatever you do, DO NOT WRITE YOUR WIFE'S SIGNATURE yourself. That's technically check fraud and could cause huge problems. I work at a bank and see people try this all the time with joint tax refunds. Either have your wife properly endorse it and mail it back, or contact the IRS to reissue.

I had this exact same situation two years ago with my husband working overseas. Here's what worked for me: First, call your bank directly and ask to speak with someone in their treasury or specialized deposits department, not just a regular teller. Many banks have specific procedures for joint tax refund checks when one payee is abroad, but the front-line staff often don't know about them. Second, the IRS actually has a form (Form 8379 - Injured Spouse Allocation) that can help in some situations, though it's typically used for different circumstances. More importantly, you can request the IRS reissue the check in your name only by explaining your spouse's non-resident status. Third, if your wife can get to a US consulate or embassy, they might be able to help with notarized documentation that your bank would accept. Some banks will accept consular-witnessed endorsements. The key is being persistent and escalating to supervisors who have authority to make exceptions. Don't give up after talking to just one person - banks deal with this more often than you'd think, especially with military families and international marriages. Whatever you do, definitely don't try to forge her signature as others have mentioned. The paper trail and your honesty about the situation will actually work in your favor with both the bank and IRS.

Having been through a similar transition from academia back to practice, I'd recommend starting with a comprehensive assessment of what services you'll actually be providing. The $225/hour from 2015 is definitely outdated - that would be closer to $275-300 today just from inflation alone. For the Midwest market you're describing, I'd suggest positioning yourself around $350/hour for tax planning and advisory work, with potentially lower rates for routine bookkeeping tasks. Your academic background actually gives you an advantage - you've stayed current with tax law changes that many practitioners struggle to keep up with. One approach that worked well for me was offering an initial consultation at a reduced rate ($200-250) to demonstrate your value and knowledge, then transitioning to full rates once they see what you bring to the table. High-net-worth clients often care more about competence and responsiveness than saving $50/hour, especially if their previous CPA was reliable. Also consider that teaching experience translates well to client education and communication - something wealthy clients particularly value when dealing with complex tax situations.

Based on my experience serving high-net-worth clients in the Midwest, I'd strongly recommend considering the $350-375/hour range that others have mentioned. However, don't overlook the importance of having the right tools and resources to justify those premium rates. One challenge I faced when transitioning to serve wealthy clients was the complexity of their tax situations often requiring immediate clarification from the IRS. Traditional methods of contacting the IRS were eating into my billable hours and frustrating clients who expected quick resolutions. I've found that having reliable ways to quickly access IRS guidance has become essential for maintaining the level of service these clients expect. When you're charging premium rates, clients want answers within days, not weeks. The ability to efficiently handle complex inquiries and provide definitive guidance rather than "I'll get back to you after I spend hours trying to reach someone at the IRS" is what separates premium-tier service from standard practice. Your academic background actually positions you well here - you understand the technical aspects, and now it's about having the operational efficiency to deliver that expertise promptly. The combination of deep knowledge and responsive service is what allows you to command those higher Midwest rates for high-net-worth clients.

Has anyone dealt with this for an installment sale? I'm selling my rental property with owner financing (buyer paying me over 10 years), and I'm confused about how the bulk sales withholding works in this case. Do they withhold from each payment I receive or just the down payment?

Just wanted to add something that might help others - timing is crucial with bulk sales withholding exemptions. I learned this the hard way when selling my duplex in Illinois last year. Most states require you to submit exemption applications 10-30 days before your scheduled closing date. I waited until 5 days before closing to apply and my exemption was still being processed when we were supposed to close. We had to delay the closing by two weeks, which cost me extra carrying costs and almost killed the deal when the buyer got frustrated. The lesson: start the exemption process as soon as you have a signed purchase agreement, not when you're getting close to closing. Even if you think you might not qualify for an exemption, it's worth applying early because the worst case is they deny it and you're back to the standard withholding anyway. Also, some states have emergency or expedited processing for exemptions if you're close to closing, but they usually charge extra fees (mine was $150 for expedited processing in Illinois). Much better to plan ahead!

I'm dealing with almost the exact same situation! Got married in August and joined my husband's family HDHP in September after having a general-purpose FSA through my old employer for the first 8 months of the year. Reading through all these responses has been super enlightening - I had no idea about the FSA creating HSA ineligibility for the entire tax year even without overlap. My benefits administrator told me I could use the last month rule for the full family amount, but it sounds like that's incorrect based on what everyone is saying here. So for my situation, would it be: Individual limit for my husband (Jan-Aug) + Family limit for both of us (Sep-Dec)? That would be roughly ($4,150 ÷ 12 × 8) + ($8,300 ÷ 12 × 4) = $2,767 + $2,767 = $5,534 total? This is such a frustrating rule, but I definitely don't want to deal with penalties and audits. Thanks to everyone for sharing their experiences - it's really helpful to see how others navigated this!

Just wanted to add my experience as another data point - I had a similar FSA-to-HSA transition situation three years ago and initially made the mistake of contributing the full family amount thinking the last month rule would cover me. The IRS actually caught this during a routine correspondence audit about 18 months later. They sent a letter asking for documentation about my HSA eligibility throughout the tax year. When I provided my FSA and insurance records, they determined I had overcontributed by about $2,400. I had to pay income tax on the excess contribution plus a 6% excise tax for each year it remained in the account. The process was a hassle but not the end of the world - I was able to remove the excess contribution and avoid ongoing penalties. The lesson I learned: always err on the side of caution with HSA contributions, especially in transition years. The prorated calculation everyone's discussing here is definitely the safe approach. Better to contribute less and avoid penalties than to risk an audit and the associated headaches. If you're unsure about your calculation, consider consulting a tax professional who specializes in HSAs. The few hundred dollars in consultation fees can save you thousands in penalties and interest down the road.